Founding Executive Director

Cypress Junction Montessori (CJM) is seeking a committed individual who wants to make a difference in the lives of young children, their families and the entire Winter Haven community. CJM is a non-profit school for children aged three to 8th grade with extended care and summer programs. CJM will be located in Winter Haven in Central Florida, 5 minutes from Legoland and 45 minutes from Disney. Please visit our website at for more information.

As we open our doors for the first time in August of 2016, the founding executive director will have a profound impact on the development, management, and ultimate success of this start-up school. Reporting to the Board of Directors, this is a full-time entrepreneurial leadership position starting June 1st.

The Executive Director must be a dynamic and competent leader. He/she will provide leadership for and management of school operations, business management, student support services, and community involvement. The ED will implement and uphold the school’s mission and guiding principles and maintain professionalism in the following areas: organization, relationship with the Board of Directors, planning and analysis, fiscal management, personnel, and community relationships.

Specific duties includes, but are not limited to:

  • Demonstrating the passion and work ethic necessary to start-up and maintain a successful Montessori school. This includes being available during core school hours and the majority of After Care hours and summer programing.
  • Communicating and collaborating effectively with the Board of Directors, teachers and staff, parents, and the community.
  • Managing the school in a fiscally responsible manner; managing the budget and budgeting process to ensure the continued success of the school, including fundraising.
  • Continuing strategic planning and implementation to ensure that the school’s needs, as it relates to resources, capital needs, and educational delivery, are met or exceeded.
  • Recruiting, retaining, and developing an effective and diverse faculty and staff
  • Developing a strategic marketing plan to provide a clear and concise message, and oversees execution of marketing and media relations.
  • Serving as primary spokesperson to all audiences (government, media, funders, and community partners).
  • Supporting the Principal as he/she executives his/her responsibilities.

Minimum Qualifications:

  • A strong working knowledge of and belief in the Montessori Method and a dedication to complete a Montessori Leadership Program within 2 years.
  • A bachelor’s degree from an accredited college or university.
  • 5 years supervisory or administrative experience in a school or business.
  • Experience managing finances for a business (preferably a school or non-profit.)

Preferred Qualifications:

  • Certification from AMI (Association Montessori Internationale), AMS (American Montessori Society), Montessori Accreditation Council for Teacher Education, or other widely recognized Montessori program.
  • Prior teaching or other experience working with children on a professional or volunteer basis
  • Supervisory and administrative experience in a Montessori or other educational setting.
  • 1+ years experience working in a leadership role at a school.
  • 10 years of successful supervisory and administrative experience.
  • A master’s degree or higher from accredited college or university, preferably in the fields of Education, Public Policy, Non-Profit, Business Management or Entrepreneurship.
  • Experience working at a public charter school during the start-up phase.

Salary competitive and commensurate with experience. Benefits are included.

Cypress Junction Montessori does not discriminate in employment opportunities or practices on the basis of race, color, sex, religion, national origin, marital status, age, disability, or other basis prohibited by law.

Qualified applicants should email a current resume, educational philosophy/personal statement (in lieu of a cover letter), and three references to: